A Person Looking At A Calender, Trying To Estimate Time
A Person Looking At A Calender, Trying To Estimate Time

Gaining Confidence in Uncertainty: How to Estimate Time for High-Level Planning

Katherine Taub

by Katherine Taub

Published on June 3, 2024Updated on July 12, 2024

6 min read

Picture this: a fantastic project has landed in your pipeline. You, your fellow PMO members and the rest of your organization can’t wait for the project’s success. The dependencies surrounding this project are building up – as well as the expectations. You need a plan as to how this is all going to work. Sure, you know it’ll be a big effort, but many people are relying on you.

So, what can you tell people about the timeline? You’ll need to plan to know!

Planning is typically thought of as either low-level (bottom-up) or high-level (top-down).

Low-level planning usually involves detailing each task a project requires shortly before starting.

In contrast, high-level planning involves working with overall timelines for every project in the entire portfolio. This kind of planning generally begins anywhere from 3-12 months before a project even starts.

In this blogpost, we will focus on high-level planning.

Planning on a high level is invaluable in securing success for your project portfolio, but it does come with its own pains and gains.

High-level planning will help organizations do the following:
  • Plan the budget required per fiscal period.
  • Determine the need and timing for hiring new employees, taking into consideration the time necessary to find and onboard them.
  • Communicate the roadmap of deliverables to achieve internal goals and deadlines or those set by customers’ needs.
  • Coordinate and collaborate with multiple teams to achieve these goals and meet the deadlines.

If these points sound interesting to you, our Director of Customer Success for the AAP Region, Debbie Summerville, has compiled some of the most common challenges and their solutions so that you can more confidently estimate your projects’ timelines. Through conversations and exchanges, we’ve chosen some of the most important points. Sound interesting? Read on to learn more!

Table of Contents

1. The Disconnect between the Reality of Active Projects and High-Level Plans

If active projects start changing their scope, or you learn that the estimated work will take less time to complete than expected, it may initially make sense to start work on new projects in your pipeline.

However, if you don’t have an overview of the potential impact on the portfolio level, you may be counting your chickens before they hatch.

In other terms, adding more active projects will inevitably introduce resource constraints on another ongoing project.

Debbie Tip Bulb

Debbie’s Fix?

You can foresee this sort of problem through planning on a high level! Start to understand the true impact of changing schedules by playing out what-if scenarios. If you can see the way adjustments change your plans in real time, it’s much easier to be ready to change in the moment.

Meisterplan has got you covered with our scenario comparison feature. You can see what your portfolio would look like if you added another project without affecting any plans permanently. This helps you understand what both your allocations and financials would look, allowing you to proceed with caution and confidence. (And, if you’re not using Meisterplan’s scenario what-if modeling, then talk to us!)

2. The Disconnect between Management and High-Level Plans

There is often a disconnect between management and the plans they are presented, as they aren’t always the most accurate. The most optimistic of upper management may operate under the assumption that these estimates are more solid than they are, especially when it comes to budgeting.

This issue is then made even worse by project managers lacking the required language to talk about the future. They may not want to promise too much, but they are also optimistic and excited about what is to come.

This confusion can also lead to issues regarding project success. For example, management may use these initial optimistic estimates as metrics against which to judge success; it may, however, not look the same for the teams working on them.

debbie-tip-gantt

Debbie’s Fix?

This one is two-fold: first, it’s totally acceptable to guide your management in understanding the accuracy of your estimations. Be open, honest and clear! Speak in ranges of time (i.e., 12 – 24 months instead of 15 months) so that there are no misunderstandings about exact dates.

Second, make sure everyone knows that high-level planning estimations are there to help you plan your portfolio, not to judge the success of projects. Don’t penalize a project just because it does not measure up to the estimates. There should be a clear understanding that estimation is a tool for scheduling, not for judging and grading.

And, with Meisterplan’s actuals features, it’s easy to see how realistic your plans really were, and then adjust for the future. You can compare your estimates for both allocations and financials and use these metrics to plan more in line with your organizational goals.

3. Lack of a Common Estimating Process

Oftentimes, hiccups in the planning process can be traced back to different parties having different understandings of how to estimate. This can even happen in the same department or team.

debbie-tip-think

Debbie’s Fix?

If you feel lost in a sea of different opinions, it’s always a great idea to bring in seasoned project managers, resource managers or PMOs! It’s a wonderful learning opportunity, and they’ll definitely have some words of wisdom you can use for years to come. They’ll ask questions like:

  • Did parts of the team estimate on a high-level?
  • Did the estimated time exclude critical tasks because people misunderstood who should be estimating them?
  • Were the estimates based on past knowledge or wild guesses?

Estimating on a high-level is a skill that you need to cultivate, and we’re more than happy to help you grow it. Our dedicated Customer Success managers are always excited to help you build out a common estimating process for your entire organization that is sustainable for years to come. 

4. You Have No Time to Spare

If you use an estimation method which requires team members give their best guesses as to how long a task will take, like bottom-up, it’s hardly surprising that people don’t have the spare time to plan. Unfortunately, these people are the subject matter experts who can probably give you the best estimate of how long their work will take

Taking subject matter experts away to estimate at a low-level before even knowing if the project will be approved is a fool’s errand. This can also easily lead to delays and bottlenecks.

debbie-tip-speech-bubble

Debbie’s Fix?

High-level planning can solve this challenge, but only if those doing it are well-versed in the skill. However, the more people work on estimating time, the better they get at it. With that, the process can soon become expedient.

In Meisterplan’s Team Planner, it’s easy to see who has a little time to spare; you can quickly allocate time for your SMEs to step away from ongoing projects to plan with you, taking some stress out of the process!

Want to Learn More?

This is just the beginning of homing in on your high-level planning and time skills. With the right tools and frame of mind, you can plan more confidently and see real success in your portfolio.

Intrigued? Debbie Summerville is happy to have a personal meeting with you to show you how your organization could reap the benefits of more accurate time estimation. You may be surprised about what you can achieve.

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